Pronounced Catalytic Effect of a Micellar Solution of Sodium Dodecyl Sulfate (SDS) on the Efficient C-S Bond Formation via an Odorless Thia-Michael Addition Reaction through the in situ Generation of S-Alkylisothiouronium Salts

A pronounced catalytic effect of sodium dodecyl sulfate (SDS) was observed on the in situ production of S-alkylisothiouronium salts via the reaction of primary, allyl and benzyl halides with thiourea in SDS droplets .Hydrolysis of the generated S-alkylisothiouronium salts in the palisade layer of the droplets produces the corresponding thiol moieties which are immediately added to the electron-deficient olefins that are present in the micellar core to produce the thia-Michael adducts. The entire route is an almost odorless process. The yields of the products are good to excellent and the method is applicable to large-scale operation without any problem.